Description

4-(1,1-Dimethylethyl)-1H-imidazole-5-carboxaldehyde (CAS No. 714273-83-3) is a high-purity heterocyclic aldehyde with the molecular formula C₈H₁₂N₂O. This compound, also known as 5-tert-butyl-1H-imidazole-4-carbaldehyde, features a reactive formyl group (–CHO) attached to the imidazole ring, making it a versatile intermediate for organic synthesis and pharmaceutical research. Its tert-butyl substituent enhances steric and electronic properties, enabling selective modifications in complex molecular architectures. Ideal for use in cross-coupling reactions, nucleophilic additions, and as a precursor for bioactive molecules. Supplied as a crystalline solid with ≥95% purity (HPLC), ensuring consistency for demanding laboratory applications. Store under inert conditions at 2-8°C to maintain stability.

Properties

• CAS Number: 714273-83-3
• Complexity: 151
• IUPAC Name: 5-tert-butyl-1H-imidazole-4-carbaldehyde
• InChI: InChI=1S/C8H12N2O/c1-8(2,3)7-6(4-11)9-5-10-7/h4-5H,1-3H3,(H,9,10)
• InChI Key: FSTXHTKEZGSDNN-UHFFFAOYSA-N
• Exact Mass: 152.094963011
• Molecular Formula: C8H12N2O
• Molecular Weight: 152.19
• SMILES: CC(C)(C)C1=C(N=CN1)C=O
• Topological: 45.8
• Monoisotopic Mass: 152.094963011
• Synonyms: 714273-83-3, 5-tert-Butyl-1H-imidazole-4-carbaldehyde, G5SL9KJW4A, 4-(1,1-dimethylethyl)-1H-Imidazole-5-carboxaldehyde, 1H-Imidazole-5-carboxaldehyde, 4-(1,1-dimethylethyl)-, 816-001-1, 939-667-6, 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, 1H-Imidazole-4-carboxaldehyde, 5-(1,1-dimethylethyl)- (9CI), 5-(tert-Butyl)imidazole-4-carbaldehyde, 4-(tert-Butyl)-1H-imidazole-5-carbaldehyde, 4-(2-Methyl-2-propanyl)-1H-imidazole-5-carbaldehyde, MFCD14583325, 1H-Imidazole-4-carboxaldehyde, 5-(1,1-dimethylethyl)-, UNII-G5SL9KJW4A, SCHEMBL65609, SCHEMBL67583, FSTXHTKEZGSDNN-UHFFFAOYSA-N, BCP07365, AKOS023876658, AKOS023876663, DH-0720, 4-(t-butyl)-1h-imidazole-5-carbaldehyde, 5-(t-butyl)-1h-imidazole-4-carbaldehyde, 5-tert-butyl-3H-imidazole-4-carbaldehyde, SY225057, DB-074430, CS-0085749, Y10245, A1-03262, 5-(1,1-Dimethylethyl)-1H-imidazole-4-carboxaldehyde

Application

4-(1,1-Dimethylethyl)-1H-imidazole-5-carboxaldehyde serves as a key building block in medicinal chemistry for the synthesis of imidazole-based drug candidates, particularly targeting enzyme inhibition. Its aldehyde functionality allows for facile condensation reactions to form Schiff bases or heterocyclic scaffolds. Researchers utilize this compound in the development of agrochemicals and corrosion inhibitors due to its robust heterocyclic core. Additionally, it finds applications in materials science as a ligand for metal-organic frameworks (MOFs).

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.